Microbial hydroxylation of (+/-)- and (-)-(2Z,4E)-5-(1 ',2 '-epoxy-2 ',6 ',6 '-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid into (+/-)- and (-)-xanthoxin acid by Cunninghamella echinulata

Authors
Okazaki, R Oritani, T Hara, Y Yamamoto, H
Citation
R. Okazaki et al., Microbial hydroxylation of (+/-)- and (-)-(2Z,4E)-5-(1 ',2 '-epoxy-2 ',6 ',6 '-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid into (+/-)- and (-)-xanthoxin acid by Cunninghamella echinulata, BIOS BIOT B, 65(4), 2001, pp. 943-946
Citations number
10
Categorie Soggetti
Agricultural Chemistry","Biochemistry & Biophysics
Journal title
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
ISSN journal
09168451 → ACNP
Volume
65
Issue
4
Year of publication
2001
Pages
943 - 946
Database
ISI
SICI code
0916-8451(200104)65:4<943:MHO(A(>2.0.ZU;2-S
Abstract
Microbial hydroxylation of (+/-)-(2 Z, 4E)-5-(1', 2'-epoxy-2', 6', 6' -trim ethylcyclohexyl)-3-methyl-2, 4-pentadienoic acid (3a) with Cercospora cruen ta, a fungus producing (+)-abscisic acid, gave a four-stereoisomeric mixtur e consisting of (+)- and (-)-santhoxin acid (4a), and (+)- and (-)-epi-xant hoxin acid (5a) bg an HPLC an:analysis with a chiral column. Screening of t he microorganisms capable of oxidizing (+/-)-3a showed that Cunninghamella echinulata stereoselectively oxidized (+/-)-3a to xanthoxin acid (4a) with the some degree of enantioselectivity as (-)-3a to (-)-4a.